Call 800-462-2848, Every day 6am-6pm,PST

Watch Videos

Ancient Footpaths in Medieval Italy

Tuscany must be experienced up close. Taste the Brunello. See the bread toasted in a stone fireplace, glistening with freshly pressed olive oil. Look out over the Arno River winding through the patchwork landscape. Walk on the gently sloping hills of the Val d'Orcia to ancient hilltop towns. Smell the wild cypress and rosemary. Stroll through the vineyards and olive groves of Chianti. Let your eyes linger on timeless villas and imagine the possibilities. There is no better—or closer—way to experience Tuscany.

Itinerary

Days
1-2From the hamlet of Monticchiello, discover the picture-perfect landscape of the Val d'Orcia Have a look around Renaissance-style Pienza, Pope Pius II's utopian village, perhaps stopping to try the superb local pecorino cheese In springtime, the surrounding hills provide a backdrop of emerald green, while in the fall, hay bales turn the landscape a brilliant shade of gold Sample a variety of regional vintages at our hotel's exclusive tasting room Follow a quiet route up to the majestic Castello di Brolio, where Baron Bettino Ricasoli formulated the modern method of producing Chianti Classico in the 19th century.

Days
3-4Explore the heart of the Zona del Chianti From Radda, amble through pristine vineyards and pine forests en route to Gaiole in Chianti, the center of Chianti Classico wine country Learn the secrets of Tuscan cuisine at an exclusive cooking demonstration Head into the Chianti countryside and walk from one castle to the next Take a break in Vertine's cozy piazzetta to enjoy a cappuccino and observe the friendly pace of local life In Panzano, learn about ancient recipes and the region's finest meats at Dario Cecchini's renowned macelleria.

Days
5-6In the Elsa River valley, get a feel for the Colli Fiorentini (Florentine Hills), where expansive vineyards and wildflower fields greet you at every turn Savor Michelin-starred cuisine inspired by Tuscan traditions and flavors Stride along the crest to Montefioralle, birthplace of Amerigo Vespucci Hike hilly roads through oak forests and along ridges offering sweeping views that once inspired Renaissance artists.

Call 800-462-2848, Every day 6am-6pm,PST

Premiere Inns

La Bandita Townhouse

Pienza (1 night) This luxury boutique hotel, tucked inside a Renaissance-era palazzo where nuns lived for over 500 years, is refreshingly modern inside. (pool)

Relais Borgo San Felice

San Felice (2 nights) Described by the Hideaway Report as an "enchanting resort enclave set within a restored medieval hamlet fringed by olive groves and vineyards in the Chianti Classico region." A Relais & Châteaux member. (pool, spa, tennis)

Castello del Nero

Guest Reviews About This Trip

Our leaders were fabulous. The itinerary and experiences could not have been better - I can't say enough to praise this trip! Having spent a lot of time in Chianti previously, I still learned, saw and experienced new things in unusual ways. My two friends with whom I traveled feel exactly the same way. It was perfect.

Marilyn R.- Scarsdale, NY

Taking a Backroads trip is like enjoying the sweetest part of the watermelon, the planners and trip leaders trim away everything but the sweetest core of the trip. They worry about the logistics, the problem solving, so that as a guest, the most you worry about is what to order at dinner and how far to go on each daily option.

Jeff Tanji- Davis, CA

We were impressed with the comfortableness with the people, the warmth and helpfulness of the guides, the flexibility of the itinerary, the good mix of planned time and free time, the well set-up walks that were incrementally longer each day so we could "build up" a bit, the loveliness of most of the lodgings, the firsthand view of the people of Italy, and of course the beauty of the country itself. I met my personal goal of doing all of the walking, and enjoyed every minute of it. I have a lasting image of our guide, catching the attention of two boys at the side of the road who were watching us all traipse through his village. He engaged them in conversation, told them who we were, asked them about the soccer ball they were playing with, and talked them into showing us their "moves." With that little dialogue, we moved from being strangers passing through to new friends visiting with local kids. I valued a lot of the personal interaction which the guides sought out with the Italian people everywhere we went. That helped us be more a part of the country. My other favorite memory is hiking on some of the back roads up through the vineyards to a place where the countryside was laid out before us like a quilt, made up of squares of vineyards, olive groves, and forested patches. Beautiful, and memorable.

This Trip Is Rated Level 1-4

Routes For All Abilities
Every Backroads trip is designed to appeal to a wide variety of
interests and fitness levels. We know your pace may vary from one
day to the next-and your traveling companion's may differ somewhat
from yours. So we present a range of mileage options, and each
day you decide exactly what and how much you want to do.

Daily Route Options

Day

EASYGOING

ACTIVE

AVID

Level 1

Level 2

Level 3

Level 4

Level 5

miles

feet gain

miles

feet gain

miles

feet gain

miles

feet gain

miles

feet gain

1

3*

400

4*

600

2

3*

300

4*

200

6*

500

3

5*

500

6*

500

8*

800

9*

1300

4

4

500

8

1200

5

4

1000

8

1600

6

3

300

note:

The terrain on this trip includes vineyard footpaths and wooded trails.

* Includes a shuttle

Private Trips Options & Pricing

Gather your favorite people to share a Backroads adventure on a ready-to-book Private Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities.

You can pick from a large selection of dates for your group of 8 or more. Call us for date availability.

If your party has fewer than 8 guests, or if your preferred date is not available, we'll create a departure just for you.